Fluorescent Imaging Probe Targeting Mitochondria Based on Supramolecular Host–Guest Assembly and Disassembly

[Image: see text] Fluorescent dyes and probes play an indispensable role in bioimaging. The mitochondrion is one of the crucial organelles which takes charge of energy production and is the primary site of aerobic respiration in the cell. To illuminate mitochondria, a series of supramolecular fluorescent imaging probes were developed based on the host–guest assembly of 1,4-bis[2-(4-pyridyl)ethenyl]-benzene (BPEB) derivatives and cucurbituril[6] (CB[6]). These host–guest conjugates can be efficiently internalized into cells due to their water solubility and target mitochondria according to their positive charges. In response to the intracellular microenvironments, these conjugates start dynamic disassembly. The released BPEBs show a highly hydrophobic feature, which can crystallize to form fluorescent solids that illuminate the mitochondria. The intracellular disassembly of the host–guest probes was evidenced by fluorescence lifetime imaging in situ. These smart mitochondrion-targeting fluorescent imaging probes can be available to investigate the structures and functions of mitochondria, which are of great significance in the intracellular dynamic transformation of supramolecular assemblies.